17 Best Road Trip Stops from Portland To Bend, Oregon

If you’re heading to the Pacific Northwest and you have a weekend to spare, a road trip from Portland to Bend, Oregon should be on your to-do list. Many travelers headed to Bend, OR as their final destination tend to fly into PDX in Portland, OR. From there, the drive from Portland to Bend (or vice versa) can easily be tackled in 3 hours.

But why would you want to make that drive without stopping to see some of the awesome spots, hikes, and sights in between? The drive from Portland to Bend is so scenic. You’ll pass by various types of scenery, starting with the densely forested atmosphere of the Portland area all the way to the high desert flora and fauna of Central Oregon. To help you make the most of your trip, we’re sharing a complete list of our favorite stops to explore along the way from Portland to Bend.

This post may contain affiliate links. You won’t be paying a cent more, but in the event of a sale, the small affiliate commission I receive will help keep this blog running/pumping out useful and free content. Thanks a lot!

Portland to Bend Road Trip - Travels With Elle

ROAD TRIP PREPARATION: RENTAL CARS

If you don’t have a car or don’t have a reliable car you trust to get you out of Portland and back in one piece, I suggest you pick up a rental car for your road trip.

We like to rent from Hertz. Why? Well with their Hertz Gold Plus Rewards program (completely free to join), you’ll get counter-free pickup at select locations, and even mobile alerts with your exact rental car and its location before you arrive. There’s a Hertz location at the PDX airport, as well as two other locations within the city. Book your rental car with them here.

If you are more the type to compare prices between rental car companies, use Priceline’s rental car search. Not only does the tool allow you to compare rental car prices, but most of the time you can book with no prepayment and no cancellation fees.

Arizona Road Trip - The Perfect 4 Day Itinerary

ROAD TRIP PREPARATION: LODGING/HOTELS

If you’re a planner like me, you’re probably going to want to book all your lodging before you leave. I don’t know about you, but the thought of not having a place to stay (or paying an arm and a leg to get a room last-minute) just makes me uneasy.

Be sure to book your lodging before you leave, or as soon as possible really, especially if you’re planning on staying at a specific hotel or yurt that you’ve been eyeing for some time.

If you are more of a spontaneous traveler, get the HotelTonight app. HotelTonight offers steeply discounted hotel prices for those last-minute bookings, perfect for spontaneous road trippers.

DEAL ALERT! Use code ELEUNG63 for $25 off on your first booking.


ROAD TRIP PREPARATION: ROAD CONDITIONS

Right before your trip, check Google Maps or TripCheck (by the Oregon Department of Transportation) before you hit the road.

We actually like TripCheck a little bit more for this exercise, because not only does it provide you with live road condition information, but it also gives you live weather alerts as well. There are even live cameras you can check out to see exactly how snowy a mountain pass may be or how bad the traffic is in the city. Though not as detailed as within Oregon, the highway condition information even extends to nearby states!


ROUTES FROM PORTLAND TO BEND

There are a few routes you could take to get to Bend from Portland (or Portland from Bend), but this list focuses on the stops along these two main routes— taking US-26 all the way down and passing Mount Hood vs. taking I-84 east through the Columbia River Gorge National Scenic Area, then down to US-26.

What’s the difference? Well first off, let’s review what you’ll see along both routes.

  • I-84 to US-26 – You’ll be going through the Columbia River Gorge to Hood River, where you’ll then take the 35 down to US-26 E and finally along US-97 S to Bend. This route is longer and more time consuming than the more direct path below.
  • US-26 – More of a straight-shot to Bend from Portland, which will save you time and miles on your car. You won’t be passing the Columbia River Gorge or Hood River, but you’ll pass Mount Hood and everything thereafter.

The mileage and duration of your trip will depend on which route you take. If you go with the longer, more scenic route of I-84, you’ll be adding on another 50 miles, but a 50 miles well worth it. The total travel time really depends on how long you stop at each of the pitstops on your itinerary!

I’d recommend going the longer route if you haven’t had the chance to explore the Columbia River Gorge or the town of Hood River yet. If you’ve been blessed to have explored the Columbia River Gorge before, then why not take the US-26 route and check out some new sights along the way?


17 BEST ROAD TRIP STOPS FROM PORTLAND TO BEND

PORTLAND

Portland is a bustling city in Oregon and is one of the greenest cities in the world. Portland prides itself on embracing weirdness, which makes this city so fun to explore. There are tons of quirky neighborhoods to explore, each with their own unique atmosphere and personality. The food truck scene is popping, as are the coffee and craft beer scenes. If you’re starting (or ending) your road trip in Portland, make sure you have at least three extra days to eat, drink, and explore the city of Portland!

Read more: The Best Neighborhoods To Visit In Portland, Oregon and 35+ Affordable, Unique, and Off The Beaten Path Things To Do in Portland

MCMENAMINS EDGEFIELD

McMenamins Edgefield is so much more than a historic hotel. This property is 74-acres large and located only 20 minutes away from downtown Portland. Formerly a poor farm during the Great Depression, McMenamins is a wonder to see and explore. It’s so expansive there is even a visitor’s guide and map of the property available to visitors.

Seriously, the estate is huge! You could easily spend a few hours wandering about the extensive gardens (glass of wine or a pint of beer in hand), play golf, visit the glass/pottery shop, distillery, and winery, take a seat and enjoy one of the many bars, eat lunch in the outdoor courtyards, watch a recent-run movie in the theater, listen to live music, and explore the gift shop. If you’re a hotel guest here, you can also take advantage of the beautiful soaking pool next to the tea bar.

COLUMBIA RIVER GORGE

The Columbia River Gorge is so beautiful and packed with jaw-dropping waterfalls, overlooks, and hikes that they named it a National Scenic Area. The Historic Columbia River Highway Scenic Byway is actually considered one of the most scenic drives in the country!

Along this 70-mile highway, you will have the chance to see several historic buildings, monuments, fish hatcheries, the Oneonta Gorge, and numerous waterfalls including Latourell Falls, Multnomah Falls, Wahkeena Falls, Shepperd’s Dell Falls, Bridal Veil Falls, Wahclella Falls, and Fairy Falls. Given recent fires over the years, it’s best to check their website to check for trail closures.

Read More: Things To Do In The Columbia River Gorge For A Perfect Day Trip

MULTNOMAH FALLS

It’s likely you’ve visited or at least heard of this popular waterfall in the Columbia River Gorge before. If you haven’t, it’s a must-see as you travel along the Historic Columbia River Highway Scenic Byway. It’s a quick stop off the highway and you can walk right up to marvel at the falls without even breaking a sweat. Talk about bang for your buck! You can grab lunch, ice cream, coffee, and other refreshments here as well.

Check the Multnomah Falls website for the most up-to-date updates/conditions.

HOOD RIVER

Continue along the scenic byway running alongside the Columbia River to reach your next stop, the charming town of Hood River. Hood River, also known as the windsurfing capital of the world, hosts a good amount of wineries, breweries, and restaurants.

This is the perfect place to stop for a meal or a cup of coffee. If you’re not feeling hungry, you should still get out of the car to stretch your legs, walk through the town, and peruse the lifestyle/home decor stores and gift shops.

LAVENDER VALLEY

I love this little off-the-road travel attraction! There’s nothing better than visiting a lavender farm during the summer season and going to annual lavender festivals. At Lavender Valley, you can wander the lovely lavender fields, cut and pick your own lavender, and explore the little gift shop after you’ve enjoyed your stroll through the grounds.

The view of Mt Hood is as intoxicating as their fragrant fields! No lie, the view by far is the best thing here and certainly does not disappoint.

If you’re looking for an alternative, there are other lavender farms in the area including Hood River Lavender Farm.

Address: 5965 Boneboro Rd, Mt Hood, OR 97041

RAMONA FALLS

One of the most beautiful waterfalls in the entire Northwest is just a quick hike away on your route from Portland to Bend.  The iconic 7-mile roundtrip hike on Ramona Falls Loop Trail provides stellar views of Mt. Hood and the grand Ramona Falls.

The trail itself is relatively easy, but the hike requires either crossing the Sandy River on fallen logs, rock hopping, or trudging through the river. If river crossings aren’t your thing, maybe skip this stop. It’s quite an adventure and totally worth it when you get to feast your eyes on Ramona Falls flowing down 120 feet of sheer basalt rock.

GOVERNMENT CAMP

Government Camp sounds much more formal than what it is–a home base for people visiting Mount Hood and exploring the national forest that surrounds the area. “Govey,” as the locals call it, is a quaint alpine village that has plenty of eateries, watering holes, and an abundance of small-town charm. It’s an excellent place to stretch your legs and use the restroom before continuing on your road trip from Portland to Bend!

TIMBERLINE LODGE

As you approach the south side of Mount Hood, take note of the signs for the Timberline Lodge (you’ll be making a left to get there). Timberline Lodge is a magnificent historical mountain lodge, built during the Depression Era. This is yet another great place to grab a bite to eat with a side of awe-inspiring views.

This National Historic Landmark is perhaps most known as the exterior of the Overlook Hotel in Stanley Kubrick’s The Shining. It’s less than 15 minutes from Government Camp and you can expect to spend about 30 minutes to an hour here.

TRILLIUM LAKE

Just 10 minutes south of Government Camp, you’ll find the picturesque Trillium Lake sitting beautifully among the great outdoors. This lake is all about the view–featuring Mount Hood towering overhead nearby. This creates an amazing mirrored view of its snow-capped peaks, especially on a clear day.

If you have some to spare, consider doing the 1.9-mile loop hike around the lake, kayaking/paddling, fishing, or packing a picnic to enjoy here. Since motorboats are not allowed here, you’ll get an even more peaceful, enjoyable experience!

INDIAN HEAD CASINO / WARM SPRINGS INDIAN MUSEUM

A bit further south on the 26 will bring you to the Indian Head Casino as well as the Warm Springs Indian Museum. Their proximity to each other will allow you to test your luck with slot machines or table games, and experience the rich history and culture of this region after.

Visitors of The Museum at Warm Springs will experience firsthand the sounds of ancient songs and languages, the mastery of traditional craftsmen, and the sights of various cultures that make up the Confederated Tribes of The Warm Springs Reservation of Oregon. The collections of the museum are rotated throughout the year.

PETER SKENE OGDEN STATE SCENIC VIEWPOINT

Located just 9 miles north of Redmond, Peter Skene Ogden State Scenic Viewpoint is a cool roadside attraction. This brief stop boasts a dramatic view of the canyon against the Crooked River.  The two sides are connected by historic bridges that create a dramatic glimpse of central Oregon’s geological and historical features.

The parkland was once owned by the Oregon Trunk Railway and was later acquired by the State between 1925 and 1930.  Eventually, the park was named after explorer Peter Skene Ogden, who entered the Crooked River Valley in 1825. This viewpoint is perfect for photography lovers and has restrooms and picnic areas.

SMITH ROCK STATE PARK

If you enjoy scenic views of towering canyons or rock climbing, Smith Rock State Park is the place for you. Rock climbers from all over the country flock to Smith Rock State Park to experience the thousands of climbing routes in the park. Here you’ll find dynamic routes that are ideal for various types of climbing and bouldering.

If climbing isn’t your thing, Smith Rock SP is still worth visiting. It’s great for trail running, hiking, wildlife spotting, and mountain biking as well. If you’re looking for a place to camp, the park also has a walk-in area for tent camping on a first-come, first-served basis.

Pro Tip: Smith Rock State Park is a popular attraction, and with that comes potential challenges with parking, especially during the peak season and on weekends. If you want to beat the crowds, visit on a weekday or try to get there before 8am on weekends. The parking/day-use fee costs $5.

Smith Rock SP - Things to Do in Bend, Oregon - Travels With Elle

CRESCENT MOON ALPACA RANCH

I added this to the list in hopes that anyone reading this is also in love with alpacas as much as I am. At the alpaca ranch, you’ll get the chance to feed the adorable alpaca as well as enjoy the alpaca boutique. It’s only 8 minutes away from Smith Rock, how can you say no?

It’s a fun place to stop, especially if you love animals or are traveling with children. You can expect to spend 45 minutes to 1 hour here.

We missed this on our last road trip, but we’re definitely making it a priority the next time we road trip to Bend, OR!

REDMOND

Redmond is a hub in the high desert along the 26 with a rejuvenated downtown, a growing beer scene, and lots of recreational activities to enjoy. Head to Downtown Redmond for a light stroll among fine dining restaurants, boutiques, bookstores, and cafes. You’ll also find a few breweries in Redmond including Kobold, Initiative, Cascade Lakes, and Wild Ride.

For family-friendly fun, check out Splash Park or the ice rink in the heart of the city. Near the airport is the Deschutes Fair & Expo Center, which hosts a wide range of events, concerts, trade shows, automobile shows, and more. Redmond is also where the Deschutes County Fair & Rodeo is held in August.

SISTERS

Looking for another high desert town to explore? When you pull into the Old West town of Sisters, OR, you’ll feel like you’ve just been transported back in time. This friendly little town in the foothills of the Cascade Mountains attracts visitors for its natural beauty as well as annual celebrations like the Sisters Rodeo (June), the Sisters Quilt Show (July) and the Sister Folk Festival (September).

Take a stroll down main street, hike the nearby trails, and enjoy the Wild West village atmosphere of Sisters.

BEND

Welcome to Bend, you made it through your road trip! If you didn’t know, Bend, Oregon is an absolute outdoor haven all year round. Summers are ideal for hiking, biking, rock climbing, and water sports, while winters are perfect for skiing or snowboarding on Mt. Bachelor. It’s the ultimate land of outdoor adventure, and you can’t forget about the craft beer tasting! Seriously, the sheer amount of fun you can have here is unreal.

There’s a lot to do within the city limits and even more to do outside of them. Check out our full list of 25+ things to do in Bend here.


WHERE TO STAY IN BEND, OR

We love staying in Bend whenever we get the chance! Our top recommendations include these super-stylish and affordable hotels:

  • LOGE Bend – Features stylish, rustic rooms; LOGE provides city bikes that are complimentary for use and offers evening entertainment and a shared kitchen.
  • Riverhouse on the Deschutes – A clean, spacious, pet-friendly hotel featuring a restaurant, seasonal outdoor pool, hot tub, fitness center, and a bar. Downtown Bend is 5 minutes’ drive away.
  • Pine Ridge Inn – Located 2 miles from Downtown Bend, Pine Ridge Inn is just 1 mile away from the Old Mill District. They offer very open and spacious suites with king-sized beds and a sofa bed. They are pet-friendly and offer an awesome free breakfast.

PORTLAND TO BEND ROAD TRIP: ESSENTIAL PACKING LIST

Aside from the normal clothing and toiletries you’d pack for any regular trip, here are the things I’d recommend you not leave home without for your Portland to Crater Lake road trip:

  • License and registration | This is a no-brainer, but always good to check you have all documents before it’s too late and you get too far away from home. Do NOT leave home without them. They are road trip essentials!
  • Spare Tire | In addition to carrying a spare tire with you, don’t forget to check your current tire conditions before you set off as well.
  • Roadside Emergency Kit | You never know what kind of car trouble you may encounter on the road. This kit contains 42 roadside emergency components, including jumper cables, an aluminum flashlight and batteries, 2-in-1 screwdriver, duct tape, poncho, cable ties, bandages, towelettes, and zipper-lock bags.
  • Trunk Organizer | With any road trip comes lots and lots of stuff to pack. Keep your road trip essentials organized with a trunk organizer. Not only will this make it so much easier to find what you need, but it will also lead to more space in your trunk for you to pack other necessities.
  • Flashlight | You never know when you’re going to be stranded on the road at night, out hiking late, or even exploring a dark cave. Leaving a flashlight in your car can really come in handy when you’re faced with unexpected situations.
  • Umbrella | An umbrella, particularly a wind-proof umbrella, is crucial when traveling to destinations with varying/unpredictable weather. If you have an umbrella with you, then it means the rain can’t stop you from enjoying your trip and exploring the outdoors.
  • Travel Pillow | If you have room in the car for a regular pillow, I find that they are the most comfortable for long car trips. If you need a more portable option, this memory foam travel pillow works well not only for car travel but also for camping!
  • Travel Blanket | For all your napping needs–especially if the driver likes AC and you’re trying to snuggle up for a nap. This one is packable so it won’t take up very much in your car.
  • Slip-on Sandals | Slip-on/slip-off sandals are a must for that extra comfort while sitting in the car. This allows you to make lots of stops without having to go through the process of putting your sneakers/boots back on.
  • Portable Cooler | Coolers are a must for any road-trip. Not only will you be able to keep beverages cold and refreshing, but you will also be able to keep perishables fresh. A portable hard cooler will allow you to pack picnic lunches, bring cheese and jams, and more. If you’re looking for the best cooler technology out there, the Yeti Portable Cooler is top of the line, with ColdCell Insulation that offers superior cold-holding compared to other soft coolers.
  • Swiss Army Knife | A multi-tool is great to have in any car, regardless of if you’re going on a road trip or not. It can be useful in so many situations! There have been so many instances where I’ve needed to cut something or open up hard-to-open packaging while away from home, and this has been a lifesaver.
  • First Aid Kit | It’s always good to carry a first aid kit around with you when traveling. Road trips make it easier to do this since all you need to do is toss it in the trunk! Note: This is not the same as the roadside emergency kit. 
  • Garbage Bags | Because you don’t want the inside of your car to resemble a dumpster can. Plastic bags (or garbage bags) can also be used to hold wet clothes if you get caught in the rain, go for a swim, etc.
  • GoPro | Capture all those awesome action/adventure moments with a top of the line action camera. Your regular camera or iPhone won’t be an option if you’re engaging in action sports like mountain biking, rock climbing, or whitewater rafting. For water sports, you could always get a waterproof case, but GoPro has time and time again proven to be the best for underwater photography.
  • Hiking Boots | If you plan on hiking, bring well broken-in boots with good ankle support and good traction. My all-time favorites are the Lowa Renegade GTX Mid Boots. They’re one of the lightest boots in its class, very durable, and provide out-of-the-box comfort, which is extremely important if you want to prevent blisters from the start.
  • Hiking Socks | Make sure you have a good pair of cushioned wool hiking socks. For extra toe protection and to prevent blisters from developing from skin-to-skin contact, go with a pair of Injinji toe socks.
  • Adventure Sandals | Tevas and Chacos are my go-to brands for multipurpose summer sandals. If you’re planning on spending some time on the river or at the Cascade Lakes, you should definitely consider getting adventure sandals — they’re comfortable for long-distance walking, safe for submerging in water, and super durable.
  • Waterproof Rain Jacket | A lightweight waterproof rain jacket is critical for any outdoor adventure. Since these weigh virtually nothing and are so easily packable, I recommend you carry one with you whenever you head outdoors. Depending on the weather forecast and chance of precipitation, I’ll either go with a rain shell or a puffier windbreaker. Despite the options I have here, one thing is for sure— I’m never without some sort of outer layer. My top recommendations are Marmot Men’s PreCip (for men) and The North Face Women’s Venture 2 Jacket (for women).
  • Puffy Jacket | You’re going to need layers in Central Oregon. The high desert climate brings chilly evenings year-round, even on warm summer days. You have a lot of options here, but I personally have the North Face Thermoball, and it’s kept me warm throughout my many years of outdoor adventuring!
  • Daypack | I’m a fan of the Deuter ACT Trail 30 Hiking Backpack. It has ample room for all the snacks and water you’ll need, as well as for your camera and the safety essentials for the hike.
  • Laundry Bag | Summer and outdoor activities = lots of sweaty, smelly, dirty, and worn clothes. Don’t soil your entire travel bag by mixing worn clothes with your unworn clothes! Definitely bring a laundry bag to separate your clean clothes from your dirty clothes to maintain the utmost freshness.
  • Hat, Bandana, or Buff | Sun protection is key for any outdoor destination. Keep the sun off your skin with a fancy sunhat, bandana, or a Buff. All three can be used to shield your neck or forehead from the sun. As a bonus, bandanas and Buffs can be used as headbands to keep hair and sweat off of your face. Soak your bandana or Buff then put it on your head, face, or neck for a quick cool down.
  • Travel Towel | These are light and quick-drying, which is exactly what you need when you’re hopping from a river to a car. This one here is a great option.
  • Travel Clothesline | This is a small and portable clothesline that allows you to hang up your wet clothes almost anywhere. I’ve found that it’s really handy whenever I have wet bathing suits or towels that need to be air-dried. I love it for its multi-purpose functionality!
  • Dry Bag | Another multi-purpose item on the list! Dry bags are completely necessary for keeping your dry belongings (clothes, electronics, money, etc)… dry. Don’t set foot on a kayak, boat or canoe without putting your stuff in a dry bag. Trust me, it’s better than ending up with a phone or camera submerged in water in the case where the boat tips or something. It’s also super handy for carrying around wet bathing suits and towels. Or even doubling as your laundry bag!
  • Insect Repellent Lotion | Mosquitos love hot and wet climates, so I would definitely recommend packing insect repellent with a high DEET percentage if you’re traveling in the summer and plan to be on the water. Sawyer makes some really great bug repellent products, and they’re travel-friendly too!
  • Hand Sanitizer Hand sanitizer gel or wipes are a must any time you’re going to be in contact with surfaces many other people have touched. Never leave your hotel room without it! And if you do happen to forget it, remember to wash your hands often, especially before eating or touching your face.
  • Body Wipes / Feminine Wipes | Feeling a bit gross after a hike but don’t have the time to shower right in that instant? Just whip out one of these body wipes for a quick refresher. The feminine wipes I like are infused with cucumber and aloe. Trust me, you will feel and smell so much better. Always good to have a few handy in your travel bag.
  • Headlamp / Flashlight | Being able to find your way through the wilderness or through lava caves in darkness is essential, so you should always carry a light source with you, even if you don’t plan on staying out past sunset. An LED headlamp allows you to hike hands-free and is my preferred source of light. FYI, the flashlight on your smartphone is not an adequate substitute– the light is not bright enough, plus it’ll drain your battery life, which may be critical in an emergency. Always carry extra batteries.
  • Portable Power Bank | You’re probably going to be out all day, snapping away taking pictures, GPSing to all the great breweries and eateries… the last thing you want is to be stranded with no phone battery! A portable power bank is a must-have, and Anker’s ultra-light, ultra-portable power bank is tried and true by so many travelers! I never embark on a day of exploration without it.
  • Soft Hydration Flask | Stay hydrated throughout the day with a water bottle that can go anywhere with you—and fold up when not in use. I love the packability of these bottles!
  • Medications | Motion sickness pills for those windy roads, painkillers, anti-inflammatories, etc.

Want more Oregon travel tips?

The Best Neighborhoods To Visit In Portland, Oregon

25+ Fun and Exciting Things To Do In Bend, Oregon

Things To Do In The Columbia River Gorge For A Perfect Day Trip

Leave a Comment